Plant disease controlling composition and method for controlling plant disease

ABSTRACT

The present invention provides a composition having an excellent controlling activity on plant disease. The composition comprising the compound represented by the formula (1) and one or more antibiotic fungicidal compound selected from the group (A) shows an excellent controlling activity on a plant disease. group (A): a group consisting of kasugamycin, polyoxins, streptomycin, and validamycin

TECHNICAL FIELD

The present invention relates to a plant disease controlling compositionand a method for controlling a plant disease.

BACKGROUND ART

Hitherto, there has been provided compounds as an active ingredient fora composition for controlling plant disease (see e.g., The PesticideManual—15th edition (BCPC published) ISBN 1901396188; and SHIBUYA INDEX13th Edition (SHIBUYA INDEX RESEARCH GROUP published)).

Also there has been provided a compound of the formula (1):

(see e.g., WO 95/27693 pamphlet and WO 02/10101 pamphlet).

DISCLOSURE OF INVENTION

An object of the present invention is to provide a composition having anexcellent control effect on a plant disease.

The present inventors have intensively studied to find out a compositionhaving an excellent control effect on a plant disease. As a result, theyhave found that a composition comprising a compound represented by theformula (1) and one or more antibiotic fungicidal compound selected fromthe following group (A) shows a synergistic activity, and thus has anexcellent control effect on a plant disease, and therefore the presentinvention has been completed.

The present invention provides:

-   [1] A plant disease controlling composition comprising a compound    represented by the formula (1):

and one or more antibiotic fungicidal compound selected from thefollowing group (A):

-   group (A): a group consisting of kasugamycin, polyoxins,    streptomycin, and validamycin.-   [2] The plant disease controlling composition according to the above    [1], wherein a weight ratio of the compound represented by the    formula (1) to the antibiotic fungicidal compound is that of the    compound represented by the formula (1)/the antibiotic fungicidal    compound=0.0125/1 to 500/1.-   [3] The plant disease controlling composition according to the above    [1] or [2], wherein the compound represented by the formula (1) is    that represented by the formula (1) having R− absolute    configuration.-   [4] A method for controlling a plant disease which comprises    applying each effective amount of the compound of the formula (1):

and one or more antibiotic fungicidal compound selected from thefollowing group (A) to a plant or a soil for cultivating the plant,

-   group (A): a group consisting of kasugamycin, polyoxins,    streptomycin, and validamycin.-   [5] The method for controlling a plant disease according to the    above [4], wherein the plant or the soil for cultivating the plant    is a seed.-   [6] The method for controlling a plant disease according to the    above [4] or [5], wherein a weight ratio of the compound represented    by the formula (1) to the antibiotic fungicidal compound is that of    the compound represented by the formula (1)/the antibiotic    fungicidal compound=0.0125/1 to 500/1.-   [7] The method for controlling a plant disease according to any one    of the above [4] to [6], wherein the compound represented by the    formula (1) is that represented by the formula (1) having R−    absolute configuration. [8] A use of a combination of the compound    represented by the formula (1):

and one or more antibiotic fungicidal compound selected from thefollowing group (A) for controlling a plant disease,

-   group (A): a group consisting of kasugamycin, polyoxins,    streptomycin, and validamycin.

The present invention enables to control a plant disease.

BEST MODE FOR CARRYING OUT THE INVENTION

A plant disease controlling composition of the present invention(hereinafter, referred to as a composition of the present invention)comprises a compound represented by the formula (1):

(hereinafter, referred to as an amide compound of the present invention)and one or more antibiotic compound selected from the following group(A) (hereinafter, referred to as a antibiotic compound of the presentinvention),

-   group (A): a group consisting of kasugamycin, polyoxins,    streptomycin, and validamycin.

The present amide compounds are those described in for example, WO95/27693 pamphlet and WO 02/10101 pamphlet, and thus can be preparedaccording to the method described therein.

The present amide compound has one asymmetric carbon. Herein, a compoundrepresented by the formula (1) wherein an enantiomer having R− absoluteconfiguration is enriched is referred to as the amide compound having R−absolute configuration.

The present amide compound encompasses the following compounds:

a compound represented by the formula (1) which is contained anenantiomer having R− absolute configuration in 70% and more;

a compound represented by the formula (1) which is contained anenantiomer having R− absolute configuration in 90% and more;

a compound represented by the formula (1) which is contained anenantiomer having R− absolute configuration in 95% and more.

Kasugamycin, polyoxins, streptomycin, and validamycin that used in thepresent invention are all known compounds, and are described in forexample, “The PESTICIDE MANUAL—15th EDITION (BCPC published) ISBN1901396188”, pages 685, 920, 1053 and 1187 respectively. These compoundsare either commercially available, or can be prepared by a known method.

The weight ratio of the present amide compound to the present antibioticcompound in the composition of the present invention is usually that ofthe present compound/the present antibiotic compound=0.0125/1 to 500/1,preferably 0.025/1 to 100/1, and more preferably 0.1/1 to 10/1.

Although the composition of the present invention may be a mixture asitself of the present amide compound and the present antibioticcompound, the composition of the present invention is usually preparedby mixing the present amide compound, the present antibiotic compoundand an inert carrier, and if necessary, adding a surfactant or otherpharmaceutical additives, and then formulating into the form of oilsolution, emulsificale concentrate, flowable formulation, wettablepowder, granulated wettable powder, dust formulation, granules and soon. Such formulations can be used by itself or with an addition of otherinert components as an agent for controlling a plant disease.

Usually, the composition of the present invention can contain 0.1 to 99%by weight, preferably 0.2 to 90% by weight, and more preferably 1 to 80%by weight of the present amide compound and the present antibioticcompound in total.

Examples of a solid carrier used on the formulation includefinely-divided power or particles of clay consisting of minerals (e.g.,kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay,pyrophyllite, talc, diatomaceous earth, or calcite), natural organicsubstances (e.g., corncob powder, or walnut shell powder), syntheticorganic substances (e.g., urea), salts (e.g., calcium carbonate, orammonium sulfate), synthetic inorganic substances (e.g., synthetichydrous silicon oxide) and so on. Examples of a liquid carrier includearomatic hydrocarbons (e.g., xylene, alkyl benzene, ormethylnaphtalene), alcohols (e.g., 2-propanol, ethylene glycol,propylene glycol, or ethylene glycol monoethyl ether), ketones (e.g.,acetone, cyclohexanone, or isophorone), vegetable oils (e.g., soybeanoil, or cotton oils), petroleum-derived aliphatic hydrocarbons, esters,dimethylsulfoxide, acetonitrile and water.

Examples of the surfactant include anionic surfactant (e.g., alkylsulfate salts, alkylaryl sulfate salts, dialkyl sulfosuccinate salts,polyoxyethylene alkylaryl ether phosphates, lignin sulfonate, ornaphthalenesulfonate formaldehyde polycondensation), nonionic surfactant(e.g., polyoxyethylene alkylaryl ether, polyoxyethylene alkylpolyoxypropylene block copolymer, or sorbitan fatty acid ester) andcationic surfactant (e.g., alkyltrimethyl ammonium salts).

Examples of the other pharmaceutical additives include water-solublepolymer (e.g., polyvinyl alcohol, or polyvinyl pyrrolidone),polysaccharides (e.g. arabic gum, alginic acid and salts thereof, CMC(carboxymethyl-cellulose), or xanthan gum), inorganic substances (e.g,aluminum magnesium silicate, or alumina-sol), antiseptic agent, coloringagent, and PAP (isopropyl acid phosphate), and stabilizing agent (e.g.,BHT).

The composition of the present invention can also be prepared byseparately formulating the present amide compound and the presentantibiotic compound into different formulations by the above procedures,if necessary, further diluting each of them with water, thereafter,mixing the separately prepared different formulations or the dilutesolutions.

The composition of the present invention may further contain one or moreother fungicide and/or insecticide.

The composition of the present invention is used to control a plantdisease by applying it to a plant or a soil for cultivating the plant.

The plant disease which can be controlled by the present invention isexemplified below:

Rice diseases: blast (Magnaporthe oryzae), helminthosporium leaf spot(Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani) andbakanae disease (Gibberella fujikuroi);

Diseases of barley, wheat, oats and rye: powdery mildew (Erysiphegraminis), Fusarium head blight (Fusarium graminearum, F. avenaceum, F.culmorum, F. asiatricum, Microdochium nivale), rust (Pucciniastriiformis, P. graminis, P. recondite, P. hordei), snow blight (Typhulasp., Micronectriella nivalis), loose smut (Ustilago tritici, U. nuda),bunt (Tilletia caries), eyespot (Pseudocercosporella herpotrichoides),scald (Rhynchosporium secalis), leaf blotch (Septoria tritici), glumeblotch (Leptosphaeria nodorum) and net blotch (Pyrenophora teresDrechsler);

Citrus diseases: melanose (Diaporthe citri), scab (Elsinoe fawcetti) andPenicillium rot (Penicillium digitatum, P. italicum);

Apple diseases: blossom blight (Monilinia mali), canker (Valsaceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leafspot (Alternaria alternata apple pathotype), scab (Venturia inaequalis),bitter rot (Colletotrichum acutatum) and late blight (Phytophtoracactorum);

Pear diseases: scab (Venturia nashicola, V. pirina), black spot(Alternaria alternate Japanese pear pathotype), rust (Gymnosporangiumharaeanum) and late blight (Phytophtora cactorum);

Peach diseases: brown rot (Monilinia fructicola), scab (Cladosporiumcarpophilum) and Phomopsis rot (Phomopsis sp.);

Grapes diseases: anthracnose (Elsinoe ampelina), ripe rot (Glomerellacingulata), powdery mildew (Uncinula necator), rust (Phakopsoraampelopsidis), black rot (Guignardia bidwellii), downy mildew(Plasmopara viticola) and Gray mold (Botrytis cinerea);

Diseases of Japanese persimmon: anthracnose (Gloeosporiura kaki) andleaf spot (Cercospora kaki, Mycosphaerella nawae);

Diseases of gourd family: anthracnose (Colletotrichum lagenarium),powdery mildew (Sphaerotheca fuliginea), gummy stem blight(Mycosphaerella melonis), Fusarium wilt (Fusarium oxysporum), downymildew (Pseudoperonospora cubensis) Phytophthora rot (Phytophthora sp.)and damping-off (Pythium sp.);

Tomato diseases: early blight (Alternaria solani), leaf mold(Cladosporium fulvum) and late blight (Phytophthora infestans);

Egg plant disease: brown spot (Phomopsis vexans) and powdery mildew(Erysiphe cichoracearum);

Diseases of Cruciferous Vegetables: Alternaria leaf spot (Alternariajaponica), white spot (Cercosporella brassicae), clubroot(Plasmodiophora brassicae), and downy mildew (Peronospora parasitica);

Rapeseed diseases: Sclerotinia rot (Sclerotinia sclerotiorum), blackspot (Alternaria brassicae), powdery mildew (Erysiphe cichoracearum),blackleg (Leptosphaeria maculans);

Welsh onion diseases: rust (Puccinia allii);

Soybean diseases: purple seed stain (Cercospora kikuchii), Sphacelomascad (Elsinoe glycines), pod and stem blight (Diaporthe phaseolorum var.sojae), rust (Phakopsora pachyrhizi) and phytophthora stem rot(Phytophthora sojae);

Adzuki-bean diseases: Gray mold (Botrytis cinerea), Sclerotinia rot(Sclerotinia sclerotiorum);

Kindney bean diseases: Gray mold (Botrytis cinerea), Sclerotinia rot(Sclerotinia sclero tiorum), anthracnose (Colletotrichum lindemthianum);

Peanut diseases: leaf spot (Cercospora personata), brown leaf spot(Cercospora arachidicola) and southern blight (Sclerotium rolfsii);

Garden pea diseases: powdery mildew (Erysiphe pisi);

Potato diseases: early blight (Alternaria solani) and late blight(Phytophthora infestans);

Strawberry diseases: powdery mildew (Sphaerotheca humuli);

Tea diseases: net blister blight (Exobasidium reticulatum) white scab(Elsinoe leucospila), gray blight (Pestalotiopsis sp.) and anthracnose(Colletotrichum theae-sinensis);

Cotton diseases: fusarium wilt (Fusarium oxysporum), damping-off(Rhizoctonia solani);

Tabacco diseases: brown spot (Alternaria longipes), powdery mildew(Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downymildew (Peronospora tabacina) and late blight (Phytophthora nicotianae);

Sugar beet diseases: Cercospora leaf spot (Cercospora beticola), leafblight (Thanatephorus cucumeris), Root rot (Aphanidermatum cochlioides);

Rose diseases: black spot (Diplocarpon rosae) and powdery mildew(Sphaerotheca pannosa);

Chrysanthemum diseases: leaf blight (Septoria chrysanthemi-indici) andwhite rust (Puccinia horiana);

Various plants diseases: diseases caused by Pythium spp. (Pythiumaphanidermatum, Pythium debarianum, Pythium graminicola, Pythiumirregulare, Pythium ultimum), Gray mold (Botrytis cinerea), Sclerotiniarot (Sclerotinia sclerotiorum),

Japanese radish diseases: Alternaria leaf spot (Alternariabrassicicola);

Turfgrass diseases: dollar spot (Sclerotinia homeocarpa), brown patchand large patch (Rhizoctonia solani); and

Banana diseases: Sigatoka disease (Mycosphaerella fijiensis,Mycosphaerella musicola, Pseudocercospora musae).

Examples of the plants to which the composition of the present inventioncan be applied are as follows:

Crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean,adzuki-bean, kindney bean, peanut, buckwheat, beet, rapeseed, sunflower,sugar cane, and tobacco, etc.;

Vegetables: solanaceous vegetables (eggplant, tomato, pimento, pepper,and potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin,zucchini, water melon, melon, and squash, etc.), cruciferous vegetables(Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage,cabbage, leaf mustard, broccoli, and cauliflower, etc.), asteraceousvegetables (burdock, crown daisy, artichoke, and lettuce, etc.),liliaceous vegetables (green onion, onion, garlic, and asparagus),ammiaceous vegetables (carrot, parsley, celery, and parsnip, etc.),chenopodiaceous vegetables (spinach, and Swiss chard, etc.), lamiaceousvegetables (Perilla frutescens, mint, and basil, etc.), strawberry,sweet potato, Dioscorea japonica, and colocasia, etc.;

Flowers;

Foliage plants;

Turfgrass;

Fruits: pomaceous fruits (apple, pear, Japanese pear, Chinese quince,and quince, etc.), stone fleshy fruits (peach, plum, nectarine, Prunusmume, cherry fruit, apricot, and prune, etc.), citrus fruits (Citrusunshiu, orange, lemon, lime, and grapefruit, etc.) nuts (chestnut,walnuts, hazelnuts, almond, pistachio, cashew nuts, and macadamia nuts,etc.) berrys (blueberry, cranberry, blackberry, and raspberry, etc.),grape, kaki fruit, olive, Japanese plum, banana, coffee, date palm, andcoconuts, etc.; and

Trees other than fruit trees: tea, mulberry, flowering plant, roadsidetrees (ash, birch, dogwood, Eucalyptus, Ginkgo biloba, lilac, maple,Quercus, poplar, Judas tree, Liquidambar formosana, plane tree, zelkova,Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, and Taxuscuspidate), etc.

The aforementioned “plants” include plants which resistance has beenimparted by genetic recombination.

Exemplary embodiments of the composition of the present invention are asfollows:

a composition comprising the present amide compound and kasugamycinwherein a weight ratio thereof is that of the present amidecompound/kasugamycin=0.0125/1 to 500/1;

a composition comprising the present amide compound and kasugamycinwherein a weight ratio thereof is that of the present amidecompound/kasugamycin=0.025/1 to 100/1;

a composition comprising the present amide compound and kasugamycinwherein a weight ratio thereof is that of the present amidecompound/kasugamycin=0.1/1 to 10/1;

a composition comprising the present amide compound and polyoxinswherein a weight ratio thereof is that of the present amidecompound/polyoxins=0.0125/1 to 500/1;

a composition comprising the present amide compound and polyoxinswherein a weight ratio thereof is that of the present amidecompound/polyoxins=0.025/1 to 100/1;

a composition comprising the present amide compound and polyoxinswherein a weight ratio thereof is that of the present amidecompound/polyoxins=0.1/1 to 10/1;

a composition comprising the present amide compound and streptomycinwherein a weight ratio thereof is that of the present amidecompound/streptomycin=0.0125/1 to 500/1;

a composition comprising the present amide compound and streptomycinwherein a weight ratio thereof is that of the present amidecompound/streptomycin=0.025/1 to 100/1;

a composition comprising the present amide compound and streptomycinwherein a weight ratio thereof is that of the present amidecompound/streptomycin=0.1/1 to 10/1;

a composition comprising the present amide compound and validamycinwherein a weight ratio thereof is that of the present amidecompound/validamycin=0.0125/1 to 500/1;

a composition comprising the present amide compound and validamycinwherein a weight ratio thereof is that of the present amidecompound/validamycin=0.025/1 to 100/1; and

a composition comprising the present amide compound and validamycinwherein a weight ratio thereof is that of the present amidecompound/validamycin=0.1/1 to 10/1.

The method for controlling a plant disease of the present invention(hereinafter, referred to as the method for controlling of the presentinvention) is carried out by applying each effective amount of thepresent amide compound and the present antibiotic compound to the plantsor the soil for cultivating the plant.

Such the plants may be, for example, foliages of plant, seeds of plant,or bulbs of plant. The bulbs herein are intended to mean bulb, corm,rootstock, tubera, tuberous root and rhizophore.

In the method for controlling of the present invention, the presentamide compound and the present antibiotic compound may be appliedseparately around the same time to the plant or the soil for cultivatingthe plant, but is usually applied as the composition of the presentinvention in terms of a convenience on applying.

In the method for controlling of the present invention, examples of themethod of applying the present amide compound and the antibioticcompound include foliage treatment, soil treatment, root treatment andseed treatment.

Such the foliage treatment includes for example, a method of applyingthe composition of the present invention to a surface of the plant to becultivated by a foliage application or a stem application.

Such the root treatment includes for example, a method of soaking awhole or a root of the plant into a medicinal solution comprising thepresent amide compound and the present antibiotic compound, and a methodof attaching a solid formulation comprising the present amide compound,the present antibiotic compound and the solid carrier to a root of theplant.

Such the soil treatment includes for example, soil broadcast, soilincorporation, and irrigation of the medicinal solution to a soil.

Such the seed treatment includes for example, an applying of thecomposition of the present invention to a seed or a bulb of the plant tobe prevented from the plant disease, specifically, for example, a spraytreatment by spraying a suspension of the composition of the presentinvention in a mist form to a surface of a seed or a surface of a bulb,a smear treatment by smearing the wettable powder, the emulsificaleconcentrate or the flowable formulation of the composition of thepresent invention with added by small amounts of water or as itself to aseed or a bulb, an immerse treatment of a seed into a solution of thecomposition of the present invention for a given time, a film-coatingtreatment, and a pellet-coating treatment.

Each dose of the present amide compound and the present antibioticcompound in the method for controlling of the present invention may bevaried depending on a kind of plant to be treated, a kind or a frequencyof an occurrence of a plant disease as a control subject, a dosage form,a treatment period, a treatment method, a treatment site, a climatecondition, etc. In case of an application to a foliage of the plant or asoil for cultivating the plant, a total amount of the present amidecompound and the antibiotic compound is usually 1 to 500 g, preferably 2to 200 g, and more preferably 10 to 100 g, per 1000 m². Each dose of thepresent amide compound and the present antibiotic compound in thetreatment for seed is usually 0.001 to 10 g, and preferably 0.01 to 1 g,per 1 kg of seeds.

The emulsificale concentrate, the wettable powder or the flowableformulation, etc., is usually applied by diluting them with water, andthen spreading them. In this case, usually, each concentration of thepresent amide compound and the present antibiotic compound contain0.0005 to 2% by weight, and preferably 0.005 to 1% by weight of thepresent amide compound and the present antibiotic compound in total. Thedust formulation or the granular formulation, etc, is usually applied asitself without diluting them.

EXAMPLES

Next, the present invention is described in more detail below by thefollowing examples including formulation examples and a test example,but the present invention should not be construed to be limited thereto.

The formulation examples are given below. It is to be noted that in theformulation examples, the term “part” indicates “part by weight”.

Formulation 1

5 parts of the present amide compound, 5 parts of kasugamycin, 35 partsof a mixture of white carbon and polyoxyethylene alkylether sulfateammonium salts (weight ratio 1:1), and 55 parts of water were mixed andthe resulting solution was then subjected to fine grinding according toa wet grinding method, so as to obtain a flowable formulation. The sameabove operations were carried out with polyoxins, streptomycin, orvalidamycin instead of kasugamycin, so as to obtain various types offlowable formulations.

Formulation 2

10 parts of the present amide compound, 5 parts of kasugamycin and 1.5parts of sorbitan trioleate were mixed into 28 parts of an aqueoussolution that contained 2 parts of polyvinyl alcohol, and the mixedsolution was then subjected to fine grinding according to a wet grindingmethod. Thereafter, 45.50 parts of an aqueous solution that contained0.05 parts of xanthan gum and 0.1 part of aluminum magnesium silicatewas added to the resultant, and 10 parts of propylene glycol was furtheradded thereto. The obtained mixture was blended by stirring, so as toobtain the flowable formulation. The same above operations were carriedout with polyoxins, streptomycin, or validamycin instead of kasugamycin,so as to obtain various types of flowable formulations.

Formulation 3

10 parts of the present amide compound, 40 parts of kasugamycin, 3 partsof calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45parts of synthetic hydrous silicon oxide were fully crushed and mixed,so as to obtain wettable powders. The same above operations were carriedout with polyoxins, streptomycin, or validamycin instead of kasugamycin,so as to obtain various types of wettable powders.

The test examples are given below.

Test Example 1

To a SUS beaker are added 30 parts of the present compound (racemate), 5parts of Soprophor FLK (polyoxyethylene tristyrylphenyl ether phosphate,produced by Rhodia Nicca Ltd.), 65 parts of ion-exchange water and 150parts of glass beads (1.0 mm diameter). The mixture is subjected togrinding at a velocity of 1000 rpm with cooling to 10° C., andthereafter the glass beads are separated, so as to obtain a flowableformulation comprising the present compound (racemate).

True leaf of cucumber is punched out with cork borer to 13 mm indiameter to prepare a leaf disk. In 24 well microwell plate that isdispensed with 1 ml 0.8% water agar, the leaf disk is placed such thatthe upper side of the leaf is in an upward direction. Thereto is added20 micro liter a testing solution prepared by mixing the flowableformulation of the present compound (racemate) prepared by the aboveprocedure and a commercial liquid formulation of validamycin or acommercial wettable powders of polyoxins to a predeterminedconcentration to treat the leaf disk.

After confirming that the testing medical solution is dried, conidium ofgray mold fungus (Botrytis cinerea) is suspended into potato dextrosebroth (DIFCO) in a density of about 10⁵ conidium/mL and is thensubjected to a spray inoculation. After leaving to stand the leaf diskin a growth chamber set up at 15° C. for four days, an onset area on theleaf is measured and then calculated an onset area rate (hereinafter,referred to as an onset area rate of treated group).

The same operation is carried out with 20 micro liter water instead of20 micro liter a testing medicine solution to calculate an onset arearate (hereinafter, referred to an onset area rate of non-treated group).

A preventive value is calculated from the above onset area rate oftreated group and the onset area rate of non-treated group by thefollowing equation:

Preventive value (%)=100×(A−B)/A

wherein

A: an onset area rate of treated group

B: an onset area rate of non-treated group

The results are shown in Tables 1 and 2.

TABLE 1 treatment concentration (ppm) the present preventive amidecompound validamycin value (%) 1 2.5 0.5 100 2 1.0 5.0 100

TABLE 2 treatment concentration (ppm) the present preventive amidecompound polyoxins value (%) 1 2.5 0.5 100 2 1.0 5.0 100

Test Example 2

The same operations as described in Test Example 1 are carried out withkasugamycin or streptomycin instead of validamycin or polyoxins, so asto calculate respective preventive values.

Also for comparison, the same operations as described in Test Example 1are carried out with the exception that the testing medicine solution issubstituted with a predetermined concentration of either a flowableformulation of the present amide compound or a commercial wettablepowder of kasugamycin or streptomycin, so as to calculate respectivepreventive values.

The results are shown in Tables 3 to 4.

TABLE 3 treatment concentration (ppm) the present preventive amidecompound kasugamycin value (%) 1 2.5 0.5 100 2 1.0 5.0 100 2.5 — 56 1.0— 46 — 0.5 0 — 5.0 10

TABLE 4 treatment concentration (ppm) the present preventive amidecompound streptomycin value (%) 1 2.5 0.5 100 2 1.0 5.0 100 2.5 — 56 1.0— 46 — 0.5 0 — 5.0 10

Next, the Reference Examples are given below.

Reference Examples

For comparison, the same operations as described in Test Example 1 arecarried out with the exception that the testing medicine solution issubstituted w _th a predetermined concentration of a solution of awettable powder of validamycin or polyoxins, so as to calculate apreventive value.

The results are shown in Tables 5 to 6.

TABLE 5 treatment concentration (ppm) preventive validamycin value (%)0.5 5 5.0 10

TABLE 6 treatment concentration (ppm) preventive polyoxins value (%) 0.511 5.0 15

1. A plant disease controlling composition comprising a compoundrepresented by the formula (1):

and one or more antibiotic fungicidal compound selected from thefollowing group (A): group (A): a group consisting of kasugamycin,polyoxins, streptomycin, and validamycin.
 2. The plant diseasecontrolling composition according to claim 1, wherein a weight ratio ofthe compound represented by the formula (1) to the antibiotic fungicidalcompound is that of the compound represented by the formula (1)/theantibiotic fungicidal compound=0.0125/1 to 500/1.
 3. The plant diseasecontrolling composition according to claim 1 or 2, wherein the compoundrepresented by the formula (1) is that represented by the formula (1)having R− absolute configuration.
 4. A method for controlling a plantdisease which comprises applying each effective amount of the compoundof the formula (1):

and one or more antibiotic fungicidal compound selected from thefollowing group (A) to a plant or a soil for cultivating the plant,group (A): a group consisting of kasugamycin, polyoxins, streptomycin,and validamycin.
 5. The method for controlling a plant disease accordingto claim 4, wherein the plant or the soil for cultivating the plant is aseed.
 6. The method for controlling a plant disease according to claim 4or 5, wherein a weight ratio of the compound represented by the formula(1) to the antibiotic fungicidal compound is that of the compoundrepresented by the formula (1)/the antibiotic fungicidalcompound=0.0125/1 to 500/1.
 7. The method for controlling a plantdisease according to claim 4, wherein the compound represented by theformula (1) is that represented by the formula (1) having R− absoluteconfiguration.
 8. A use of a combination of the compound represented bythe formula (1):

and one or more antibiotic fungicidal compound selected from thefollowing group (A) for controlling a plant disease, group (A): a groupconsisting of kasugamycin, polyoxins, streptomycin, and validamycin.